US8754184B2 - Accelerated cure of isocyanate terminated prepolymers - Google Patents

Accelerated cure of isocyanate terminated prepolymers Download PDF

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Publication number
US8754184B2
US8754184B2 US12/913,888 US91388810A US8754184B2 US 8754184 B2 US8754184 B2 US 8754184B2 US 91388810 A US91388810 A US 91388810A US 8754184 B2 US8754184 B2 US 8754184B2
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US
United States
Prior art keywords
prepolymer
diisocyanate
salt
mixture
prepolymer mixture
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related, expires
Application number
US12/913,888
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English (en)
Other versions
US20110118431A1 (en
Inventor
Thomas R. Doyle
Mark P. Ferrandino
Ronald O. Rosenberg
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lanxess Solutions US Inc
Original Assignee
Chemtura Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to US12/913,888 priority Critical patent/US8754184B2/en
Application filed by Chemtura Corp filed Critical Chemtura Corp
Priority to PCT/US2010/056807 priority patent/WO2011060407A1/en
Priority to KR1020127011873A priority patent/KR101788339B1/ko
Priority to CN201080051744.6A priority patent/CN102612528B/zh
Priority to CA 2779849 priority patent/CA2779849A1/en
Priority to BR112012011515A priority patent/BR112012011515A2/pt
Priority to AU2010319998A priority patent/AU2010319998B2/en
Priority to JP2012539066A priority patent/JP2013510935A/ja
Priority to EP10779438A priority patent/EP2501736A1/en
Assigned to CHEMTURA CORPORATION reassignment CHEMTURA CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FERRANDINO, MARK P., ROSENBERG, RONALD O., DOYLE, THOMAS R.
Publication of US20110118431A1 publication Critical patent/US20110118431A1/en
Priority to US14/202,232 priority patent/US9006375B2/en
Publication of US8754184B2 publication Critical patent/US8754184B2/en
Application granted granted Critical
Assigned to BANK OF AMERICA, N.A. reassignment BANK OF AMERICA, N.A. AMENDED AND RESTATED SECOND LIEN INTELLECTUAL PROPERY SECURITY AGREEMENT Assignors: CHEMTURA CORPORATION, CROMPTON COLORS INCORPORATED, GLCC LAUREL, LLC, GREAT LAKES CHEMICAL CORPORATION
Assigned to BANK OF AMERICA, N.A. reassignment BANK OF AMERICA, N.A. THIRD LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Assignors: CHEMTURA CORPORATION, CROMPTON COLORS INCORPORATED, GLCC LAUREL, LLC, GREAT LAKES CHEMICAL CORPORATION
Assigned to GREAT LAKES CHEMICAL CORPORATION, GLCC LAUREL, LLC, CROMPTON COLORS INCORPORATED, CHEMTURA CORPORATION reassignment GREAT LAKES CHEMICAL CORPORATION RELEASE OF AMENDED AND RESTATED SECOND LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Assignors: BANK OF AMERICA, N.A.
Assigned to CROMPTON COLORS INCORPORATED, GLCC LAUREL, LLC, GREAT LAKES CHEMICAL CORPORATION, CHEMTURA CORPORATION reassignment CROMPTON COLORS INCORPORATED RELEASE OF THIRD LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Assignors: BANK OF AMERICA, N.A.
Assigned to LANXESS SOLUTIONS US INC. reassignment LANXESS SOLUTIONS US INC. MERGER AND CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: CHEMTURA CORPORATION, LANXESS SOLUTIONS US INC.
Assigned to LANXESS SOLUTIONS US INC. reassignment LANXESS SOLUTIONS US INC. MERGER AND CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: CHEMTURA CORPORATION, LANXESS SOLUTIONS US INC.
Expired - Fee Related legal-status Critical Current
Adjusted expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/1875—Catalysts containing secondary or tertiary amines or salts thereof containing ammonium salts or mixtures of secondary of tertiary amines and acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/20—Heterocyclic amines; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/20—Heterocyclic amines; Salts thereof
    • C08G18/2009—Heterocyclic amines; Salts thereof containing one heterocyclic ring
    • C08G18/2018—Heterocyclic amines; Salts thereof containing one heterocyclic ring having one nitrogen atom in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/20—Heterocyclic amines; Salts thereof
    • C08G18/2009—Heterocyclic amines; Salts thereof containing one heterocyclic ring
    • C08G18/2027—Heterocyclic amines; Salts thereof containing one heterocyclic ring having two nitrogen atoms in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/82—Post-polymerisation treatment

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
US12/913,888 2009-11-16 2010-10-28 Accelerated cure of isocyanate terminated prepolymers Expired - Fee Related US8754184B2 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
US12/913,888 US8754184B2 (en) 2009-11-16 2010-10-28 Accelerated cure of isocyanate terminated prepolymers
KR1020127011873A KR101788339B1 (ko) 2009-11-16 2010-11-16 이소시아네이트 종결된 프리폴리머의 촉진된 경화
CN201080051744.6A CN102612528B (zh) 2009-11-16 2010-11-16 异氰酸酯封端的预聚物的加速固化
CA 2779849 CA2779849A1 (en) 2009-11-16 2010-11-16 Accelerated cure of isocyanate terminated prepolymers
BR112012011515A BR112012011515A2 (pt) 2009-11-16 2010-11-16 "mistura de pré-polímero para a preparação de um elastômero de poliuretano, elastômero de poliuretano e método para preparar o mesmo".
AU2010319998A AU2010319998B2 (en) 2009-11-16 2010-11-16 Accelerated cure of isocyanate terminated prepolymers
JP2012539066A JP2013510935A (ja) 2009-11-16 2010-11-16 イソシアネート末端プレポリマーの促進された硬化
EP10779438A EP2501736A1 (en) 2009-11-16 2010-11-16 Accelerated cure of isocyanate terminated prepolymers
PCT/US2010/056807 WO2011060407A1 (en) 2009-11-16 2010-11-16 Accelerated cure of isocyanate terminated prepolymers
US14/202,232 US9006375B2 (en) 2009-11-16 2014-03-10 Accelerated cure of isocyanate terminated prepolymers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US26169909P 2009-11-16 2009-11-16
US12/913,888 US8754184B2 (en) 2009-11-16 2010-10-28 Accelerated cure of isocyanate terminated prepolymers

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US14/202,232 Division US9006375B2 (en) 2009-11-16 2014-03-10 Accelerated cure of isocyanate terminated prepolymers

Publications (2)

Publication Number Publication Date
US20110118431A1 US20110118431A1 (en) 2011-05-19
US8754184B2 true US8754184B2 (en) 2014-06-17

Family

ID=43432372

Family Applications (2)

Application Number Title Priority Date Filing Date
US12/913,888 Expired - Fee Related US8754184B2 (en) 2009-11-16 2010-10-28 Accelerated cure of isocyanate terminated prepolymers
US14/202,232 Expired - Fee Related US9006375B2 (en) 2009-11-16 2014-03-10 Accelerated cure of isocyanate terminated prepolymers

Family Applications After (1)

Application Number Title Priority Date Filing Date
US14/202,232 Expired - Fee Related US9006375B2 (en) 2009-11-16 2014-03-10 Accelerated cure of isocyanate terminated prepolymers

Country Status (9)

Country Link
US (2) US8754184B2 (ko)
EP (1) EP2501736A1 (ko)
JP (1) JP2013510935A (ko)
KR (1) KR101788339B1 (ko)
CN (1) CN102612528B (ko)
AU (1) AU2010319998B2 (ko)
BR (1) BR112012011515A2 (ko)
CA (1) CA2779849A1 (ko)
WO (1) WO2011060407A1 (ko)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10167358B2 (en) 2015-08-17 2019-01-01 Covestro Deutschland Ag Process for modifying isocyanates with use of cyclic ammonium salts as catalyst
US10577450B2 (en) 2015-09-25 2020-03-03 Lanxess Solutions Us Inc. Storage stable activated prepolymer composition

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* Cited by examiner, † Cited by third party
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CN102658057B (zh) * 2012-04-16 2014-09-10 王志军 一种新型聚氨酯分散剂及其制备方法
CN105531296B (zh) 2013-07-16 2019-10-25 巴斯夫欧洲公司 异氰酸酯预聚物组合物以及由其制备的交联的聚氨酯
JP6639939B2 (ja) * 2016-02-12 2020-02-05 ニッタ・ハース株式会社 研磨パッド、および、研磨パッドの製造方法
CN106478923B (zh) * 2016-03-10 2019-01-15 北京纽科尔斯新型建材科技有限公司 一种环保型聚氨酯塑胶跑道铺装维修材料
CN105949751A (zh) * 2016-07-06 2016-09-21 苏州亚科塑胶有限公司 一种防滑耐磨高弹性复合塑胶跑道面层的制备方法
CN106117508A (zh) * 2016-07-21 2016-11-16 山东诺威聚氨酯股份有限公司 塑胶跑道用发泡聚氨酯弹性层材料及其制备方法
CN107325261A (zh) * 2017-08-29 2017-11-07 杭州重力脚轮科技有限公司 一种1,5‑萘二异氰酸酯型聚氨酯弹性体及其制备方法和应用
KR20210044997A (ko) 2019-10-16 2021-04-26 주식회사 세호 폴리우레탄 제조용 경화제, 폴리우레탄 제조용 조성물 및 이를 이용하여 폴리우레탄을 제조하는 방법
CN112080259B (zh) * 2020-04-14 2022-04-01 西南石油大学 一种环保型超支化聚季铵盐氨基酸制成的页岩插层抑制剂
CN113136021A (zh) * 2021-04-15 2021-07-20 浙江省三门县西陈橡胶厂 Ptm轨下垫板及其加工方法
EP4347679A1 (en) 2021-06-03 2024-04-10 Carbon, Inc. Methods for the rapid production of blocked prepolymers
CN115093540B (zh) * 2022-05-24 2023-03-17 烟台瑞特橡塑有限公司 一种高硬度聚氨酯轮胎及其制备方法
CN116041660B (zh) * 2023-03-29 2023-06-30 北京大学第三医院（北京大学第三临床医学院） 一种具有抗菌活性的离子型聚氨酯及其制备方法

Citations (15)

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Publication number Priority date Publication date Assignee Title
GB1101410A (en) 1965-06-23 1968-01-31 American Cyanamid Co Polyurethane prepolymers
US3471423A (en) 1966-11-07 1969-10-07 Gen Tire & Rubber Co Polyurethane materials having biocidal properties and their production
US3899438A (en) * 1973-10-17 1975-08-12 Du Pont Simultaneous reaction and dispersion of 4,4-methylene dianiline-salt mixtures to form complexes thereof
US3900447A (en) * 1974-04-30 1975-08-19 Du Pont Thermally activated promoters for salt complex curing agents
US4075150A (en) * 1977-03-30 1978-02-21 E. I. Du Pont De Nemours And Company Composition for curing polyurethanes
US4182825A (en) 1978-10-11 1980-01-08 Thiokol Corporation Polyether based urethanes with superior dynamic properties
US4195150A (en) 1978-10-13 1980-03-25 M & T Chemicals Inc. Novel composition for preparing urethane/urea block copolymers
US4282344A (en) 1978-11-02 1981-08-04 E. I. Du Pont De Nemours And Company Polyurethane curing agent dispersion, process and product
US4330454A (en) * 1981-04-06 1982-05-18 The Goodyear Tire & Rubber Company Storable flowable polypropylene ether urethane composition
US4521545A (en) 1983-08-09 1985-06-04 Bayer Aktiengesellschaft Latent catalysts for the isocyanate polyaddition reaction
US5703193A (en) 1996-06-03 1997-12-30 Uniroyal Chemical Company, Inc. Removal of unreacted diisocyanate monomer from polyurethane prepolymers
US20030065124A1 (en) 1999-11-30 2003-04-03 Rosenberg Ronald O. High performance polyurethane elastomers from MDI prepolymers with reduced content of free MDI monomer
US20030134971A1 (en) * 1996-09-30 2003-07-17 Blount David H. Amino catalyst for polyurethane products
US6953765B2 (en) 2001-05-07 2005-10-11 Bayer Aktiengesellschaft Double metal cyanide catalysts for preparing polyether polyols
US20100256311A1 (en) * 2009-04-07 2010-10-07 Doyle Thomas R Curing compositions having low-free amounts of methylenedianiline

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Publication number Priority date Publication date Assignee Title
GB1101410A (en) 1965-06-23 1968-01-31 American Cyanamid Co Polyurethane prepolymers
US3471423A (en) 1966-11-07 1969-10-07 Gen Tire & Rubber Co Polyurethane materials having biocidal properties and their production
US3899438A (en) * 1973-10-17 1975-08-12 Du Pont Simultaneous reaction and dispersion of 4,4-methylene dianiline-salt mixtures to form complexes thereof
US3900447A (en) * 1974-04-30 1975-08-19 Du Pont Thermally activated promoters for salt complex curing agents
US4075150A (en) * 1977-03-30 1978-02-21 E. I. Du Pont De Nemours And Company Composition for curing polyurethanes
US4182825A (en) 1978-10-11 1980-01-08 Thiokol Corporation Polyether based urethanes with superior dynamic properties
US4195150A (en) 1978-10-13 1980-03-25 M & T Chemicals Inc. Novel composition for preparing urethane/urea block copolymers
US4282344A (en) 1978-11-02 1981-08-04 E. I. Du Pont De Nemours And Company Polyurethane curing agent dispersion, process and product
US4330454A (en) * 1981-04-06 1982-05-18 The Goodyear Tire & Rubber Company Storable flowable polypropylene ether urethane composition
US4521545A (en) 1983-08-09 1985-06-04 Bayer Aktiengesellschaft Latent catalysts for the isocyanate polyaddition reaction
US5703193A (en) 1996-06-03 1997-12-30 Uniroyal Chemical Company, Inc. Removal of unreacted diisocyanate monomer from polyurethane prepolymers
US20030134971A1 (en) * 1996-09-30 2003-07-17 Blount David H. Amino catalyst for polyurethane products
US20030065124A1 (en) 1999-11-30 2003-04-03 Rosenberg Ronald O. High performance polyurethane elastomers from MDI prepolymers with reduced content of free MDI monomer
US20080146765A1 (en) * 1999-11-30 2008-06-19 Rui Xie High performance polyurethane elastomers from mdi prepolymers with reduced content of free mdi monomer
US20090076239A1 (en) * 1999-11-30 2009-03-19 Rui Xie High performance polyurethane elastomers from mdi prepolymers with reduced content of free mdi monomer
US6953765B2 (en) 2001-05-07 2005-10-11 Bayer Aktiengesellschaft Double metal cyanide catalysts for preparing polyether polyols
US20100256311A1 (en) * 2009-04-07 2010-10-07 Doyle Thomas R Curing compositions having low-free amounts of methylenedianiline

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10167358B2 (en) 2015-08-17 2019-01-01 Covestro Deutschland Ag Process for modifying isocyanates with use of cyclic ammonium salts as catalyst
US10577450B2 (en) 2015-09-25 2020-03-03 Lanxess Solutions Us Inc. Storage stable activated prepolymer composition

Also Published As

Publication number Publication date
CA2779849A1 (en) 2011-05-19
US9006375B2 (en) 2015-04-14
US20110118431A1 (en) 2011-05-19
AU2010319998A1 (en) 2012-05-24
WO2011060407A1 (en) 2011-05-19
EP2501736A1 (en) 2012-09-26
JP2013510935A (ja) 2013-03-28
CN102612528A (zh) 2012-07-25
BR112012011515A2 (pt) 2016-06-07
CN102612528B (zh) 2014-09-10
US20140194588A1 (en) 2014-07-10
KR20120105442A (ko) 2012-09-25
AU2010319998B2 (en) 2015-06-11
KR101788339B1 (ko) 2017-10-19

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